Find Family Hotels in Pittsfield, MA

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Check availability on Pittsfield Family Hotels

Tonight
Dec 3 - Dec 4
Tomorrow
Dec 4 - Dec 5
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Top Pittsfield Family Hotels

Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1004)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is NT$2,935
NT$3,278 total
includes taxes & fees
Dec 17 - Dec 18
Best Western Plus Berkshire Hills Inn & Suites
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is NT$4,113
NT$4,594 total
includes taxes & fees
Dec 11 - Dec 12
Element Lenox Berkshires
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (975)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is NT$2,916
NT$3,257 total
includes taxes & fees
Dec 17 - Dec 18
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1000)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is NT$3,177
NT$3,549 total
includes taxes & fees
Dec 14 - Dec 15
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
Cozy Corner Motel

Cozy Corner Motel

2.0 star property
Williamstown
9.2 out of 10, Wonderful, (884)
"Clean, Great Staff, Quiet"
United States
john
The price is NT$2,345
NT$2,769 total
includes taxes & fees
Dec 4 - Dec 5
Cozy Corner Motel
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (64)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is NT$2,866
NT$3,202 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express

FairBridge Inn Express

2.5 star property
Pittsfield
5.4 out of 10, (810)
"Room spotless and staff helpful."
United States
William
The price is NT$2,515
NT$2,809 total
includes taxes & fees
Dec 17 - Dec 18
FairBridge Inn Express
Lobby
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

2.5 star property
Castleton-on-Hudson
8.4 out of 10, Very Good, (1001)
"Room was spotless, staff very friendly."
United States
amber
The price is NT$3,017
NT$3,349 total
includes taxes & fees
Jan 1 - 2026/1/2
Comfort Inn & Suites East Greenbush - Albany
Property amenity
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (757)
"Clean room, very courteous staff "
United States
Thomas
The price is NT$4,741
NT$5,296 total
includes taxes & fees
Dec 10 - Dec 11
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Children's play area - outdoor
Maple Terrace Motel

Maple Terrace Motel

2.5 star property
Williamstown
9.6 out of 10, Exceptional, (586)
"Reception was great, lovely beds (most important to me), great location, this place is excellent."
United States
William
The price is NT$3,108
NT$3,472 total
includes taxes & fees
Dec 4 - Dec 5
Maple Terrace Motel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Pittsfield Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Perfect "
Peter 2-night trip
Posted 2 days ago
Hotel Downstreet, an Ascend Collection Hotel

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Frequently asked questions

What's Pittsfield like for family-friendly vacations?
The historic destination of Pittsfield is a good choice if you've been thinking about a trip with your kids. The biking trails, entertainment, and lake views are just some of the things that make this a good place for family vacations. Take to the air and fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is the closest airport, or Hudson, NY (HCC-Columbia County), which is located 25.7 mi (41.4 km) from the city center.
What's the best hotel when traveling with kids to Pittsfield?
Holiday Inn & Suites Pittsfield-Berkshires by IHG is a hotel with an indoor pool and a restaurant, and it's a top choice on Expedia for families. Other choices for your family trip include Best Western Plus Berkshire Hills Inn & Suites and Holiday Inn Express & Suites Pittsfield - Berkshires by IHG.
When's the best time to book a family-friendly vacation in Pittsfield?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's there to see and do with your family in Pittsfield?
Colonial Theater, Bousquet Ski Area, and Berkshire Athenaeum are interesting attractions you and your family will enjoy exploring while you are staying in Pittsfield. Make sure you have lots of time for activities like Barrington Stage Company and Guido's Marketplace.
What's the best way for us to get around Pittsfield?
To see more of the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station. Pittsfield might not have many public transit options so consider renting a car to explore more.